MX2012011780A - Nuevos derivados de 3,3-dimetil tetrahidroquinolina. - Google Patents
Nuevos derivados de 3,3-dimetil tetrahidroquinolina.Info
- Publication number
- MX2012011780A MX2012011780A MX2012011780A MX2012011780A MX2012011780A MX 2012011780 A MX2012011780 A MX 2012011780A MX 2012011780 A MX2012011780 A MX 2012011780A MX 2012011780 A MX2012011780 A MX 2012011780A MX 2012011780 A MX2012011780 A MX 2012011780A
- Authority
- MX
- Mexico
- Prior art keywords
- dimethyl
- phenyl
- tetrahydro
- quinoline
- carboxylic acid
- Prior art date
Links
- CPSWFAQCNUAYRA-UHFFFAOYSA-N 3,3-dimethyl-2,4,4a,5-tetrahydro-1h-quinoline Chemical class C1=CCC2CC(C)(C)CNC2=C1 CPSWFAQCNUAYRA-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 180
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 9
- -1 haloalkyl cyano Chemical group 0.000 claims description 524
- 238000006243 chemical reaction Methods 0.000 claims description 157
- 239000002253 acid Substances 0.000 claims description 136
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
- DLTBAYKGXREKMW-UHFFFAOYSA-N cyclopropanesulfonic acid Chemical compound OS(=O)(=O)C1CC1 DLTBAYKGXREKMW-UHFFFAOYSA-N 0.000 claims description 65
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical group 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 36
- 150000002148 esters Chemical class 0.000 claims description 30
- 150000002431 hydrogen Chemical group 0.000 claims description 24
- 230000008569 process Effects 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
- 239000003153 chemical reaction reagent Substances 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 14
- 238000010168 coupling process Methods 0.000 claims description 14
- 238000005859 coupling reaction Methods 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- ARNALYPZOYPNAF-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline-6-carboxylic acid Chemical compound N1CCCC2=CC(C(=O)O)=CC=C21 ARNALYPZOYPNAF-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 claims description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 11
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 238000011321 prophylaxis Methods 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 208000008589 Obesity Diseases 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 235000020824 obesity Nutrition 0.000 claims description 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000005059 halophenyl group Chemical group 0.000 claims description 7
- 201000001421 hyperglycemia Diseases 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- UBQIOJKVPHVCLY-UHFFFAOYSA-N 2-(3-fluoro-5-pyrrolidin-1-ylphenyl)-3,3-dimethyl-n-methylsulfonyl-2,4-dihydro-1h-quinoline-6-carboxamide Chemical compound CC1(C)CC2=CC(C(=O)NS(C)(=O)=O)=CC=C2NC1C(C=1)=CC(F)=CC=1N1CCCC1 UBQIOJKVPHVCLY-UHFFFAOYSA-N 0.000 claims description 6
- WLNUGCHKEVDWTE-UHFFFAOYSA-N 2-[3-[(1-carboxycyclopropyl)amino]phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=1)=CC=CC=1NC1(C(O)=O)CC1 WLNUGCHKEVDWTE-UHFFFAOYSA-N 0.000 claims description 6
- LMAGDVNNBGSEHW-UHFFFAOYSA-N 3,3-dimethyl-2-[3-(3-methyl-2-oxoimidazolidin-1-yl)phenyl]-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound O=C1N(C)CCN1C1=CC=CC(C2C(CC3=CC(=CC=C3N2)C(O)=O)(C)C)=C1 LMAGDVNNBGSEHW-UHFFFAOYSA-N 0.000 claims description 6
- CMSBZDZDJWDFOW-UHFFFAOYSA-N 3,3-dimethyl-2-[3-(propan-2-ylsulfonylamino)phenyl]-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC(C)S(=O)(=O)NC1=CC=CC(C2C(CC3=CC(=CC=C3N2)C(O)=O)(C)C)=C1 CMSBZDZDJWDFOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- KCRCCWRAXNSLMX-UHFFFAOYSA-N 2-[3-[3,3-dimethyl-6-(trifluoromethyl)-2,4-dihydro-1h-quinolin-2-yl]anilino]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC1=CC=CC(C2C(CC3=CC(=CC=C3N2)C(F)(F)F)(C)C)=C1 KCRCCWRAXNSLMX-UHFFFAOYSA-N 0.000 claims description 5
- CLRBSDDSABEDHS-UHFFFAOYSA-N 3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2CC(C)(C)CNC2=C1 CLRBSDDSABEDHS-UHFFFAOYSA-N 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- STWLCBZXOGHSAR-UHFFFAOYSA-N 2-(2-fluoro-5-morpholin-4-ylphenyl)-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C(=CC=1)F)=CC=1N1CCOCC1 STWLCBZXOGHSAR-UHFFFAOYSA-N 0.000 claims description 4
- XHPXHJSQZTZYQY-UHFFFAOYSA-N 2-(3-aminophenyl)-3,3-dimethyl-n-methylsulfonyl-2,4-dihydro-1h-quinoline-6-carboxamide Chemical compound CC1(C)CC2=CC(C(=O)NS(C)(=O)=O)=CC=C2NC1C1=CC=CC(N)=C1 XHPXHJSQZTZYQY-UHFFFAOYSA-N 0.000 claims description 4
- MLBQDXURJDAIAJ-UHFFFAOYSA-N 2-(3-methoxy-5-morpholin-4-ylphenyl)-3,3-dimethyl-2,4-dihydro-1H-quinoline-6-carboxamide Chemical compound C=1C(OC)=CC(C2C(CC3=CC(=CC=C3N2)C(N)=O)(C)C)=CC=1N1CCOCC1 MLBQDXURJDAIAJ-UHFFFAOYSA-N 0.000 claims description 4
- MGIKWYOBVIJDRD-UHFFFAOYSA-N 2-(3-methoxy-5-morpholin-4-ylphenyl)-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound C=1C(OC)=CC(C2C(CC3=CC(=CC=C3N2)C(O)=O)(C)C)=CC=1N1CCOCC1 MGIKWYOBVIJDRD-UHFFFAOYSA-N 0.000 claims description 4
- DDNXSXCTQYSGNX-UHFFFAOYSA-N 2-(3-methoxy-5-morpholin-4-ylphenyl)-3,3-dimethyl-n-methylsulfonyl-2,4-dihydro-1h-quinoline-6-carboxamide Chemical compound C=1C(OC)=CC(C2C(CC3=CC(=CC=C3N2)C(=O)NS(C)(=O)=O)(C)C)=CC=1N1CCOCC1 DDNXSXCTQYSGNX-UHFFFAOYSA-N 0.000 claims description 4
- UJXJNZZDZRCULN-UHFFFAOYSA-N 2-(4-fluoro-3-morpholin-4-ylphenyl)-3,3-dimethyl-2,4-dihydro-1H-quinoline-6-carboxamide Chemical compound CC1(C)CC2=CC(C(N)=O)=CC=C2NC1C(C=1)=CC=C(F)C=1N1CCOCC1 UJXJNZZDZRCULN-UHFFFAOYSA-N 0.000 claims description 4
- CRHPLNJFAKFKND-UHFFFAOYSA-N 2-[2-[(1-carboxycyclopropyl)amino]phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C1=CC=CC=C1NC1(C(O)=O)CC1 CRHPLNJFAKFKND-UHFFFAOYSA-N 0.000 claims description 4
- SNPOVMITJXQOIU-UHFFFAOYSA-N 2-[2-[(2-fluorophenyl)sulfonylamino]phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=C1F SNPOVMITJXQOIU-UHFFFAOYSA-N 0.000 claims description 4
- DIQFWIPAOLWGTQ-UHFFFAOYSA-N 2-[2-[(3-fluorophenyl)sulfonylamino]phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C1=CC=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 DIQFWIPAOLWGTQ-UHFFFAOYSA-N 0.000 claims description 4
- SHXXXQGTUCTCDK-UHFFFAOYSA-N 2-[2-[(4-fluorophenyl)sulfonylamino]phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C1=CC=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1 SHXXXQGTUCTCDK-UHFFFAOYSA-N 0.000 claims description 4
- ONVPBYBLQAFGEU-UHFFFAOYSA-N 2-[3-(2,5-dioxopiperazin-1-yl)phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=1)=CC=CC=1N1CC(=O)NCC1=O ONVPBYBLQAFGEU-UHFFFAOYSA-N 0.000 claims description 4
- WBYPISBMRXMQPA-UHFFFAOYSA-N 2-[3-(4-tert-butylphenyl)phenyl]-6-fluoro-3,3-dimethyl-2,4-dihydro-1H-quinoline-5-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=CC(C2C(CC3=C(C(N)=O)C(F)=CC=C3N2)(C)C)=C1 WBYPISBMRXMQPA-UHFFFAOYSA-N 0.000 claims description 4
- OLQGYSIQCZVJGN-UHFFFAOYSA-N 2-[3-(dimethylamino)-5-fluorophenyl]-3,3-dimethyl-n-methylsulfonyl-2,4-dihydro-1h-quinoline-6-carboxamide Chemical compound CN(C)C1=CC(F)=CC(C2C(CC3=CC(=CC=C3N2)C(=O)NS(C)(=O)=O)(C)C)=C1 OLQGYSIQCZVJGN-UHFFFAOYSA-N 0.000 claims description 4
- QEHDPFWBLQHCRD-UHFFFAOYSA-N 2-[3-[3,3-dimethyl-6-(methylsulfonylcarbamoyl)-2,4-dihydro-1h-quinolin-2-yl]anilino]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC1=CC=CC(C2C(CC3=CC(=CC=C3N2)C(=O)NS(C)(=O)=O)(C)C)=C1 QEHDPFWBLQHCRD-UHFFFAOYSA-N 0.000 claims description 4
- LELCHWIQJUMJOV-UHFFFAOYSA-N 2-[4-fluoro-3-(2-methylpropanoylamino)phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound C1=C(F)C(NC(=O)C(C)C)=CC(C2C(CC3=CC(=CC=C3N2)C(O)=O)(C)C)=C1 LELCHWIQJUMJOV-UHFFFAOYSA-N 0.000 claims description 4
- LLMWZOFBPQSQAR-UHFFFAOYSA-N 3,3-dimethyl-2-(3-methyl-5-morpholin-4-ylphenyl)-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound C=1C(C)=CC(C2C(CC3=CC(=CC=C3N2)C(O)=O)(C)C)=CC=1N1CCOCC1 LLMWZOFBPQSQAR-UHFFFAOYSA-N 0.000 claims description 4
- FLZKHOKEKXPWED-UHFFFAOYSA-N 3,3-dimethyl-2-(3-methyl-5-morpholin-4-ylphenyl)-n-methylsulfonyl-2,4-dihydro-1h-quinoline-6-carboxamide Chemical compound C=1C(C)=CC(C2C(CC3=CC(=CC=C3N2)C(=O)NS(C)(=O)=O)(C)C)=CC=1N1CCOCC1 FLZKHOKEKXPWED-UHFFFAOYSA-N 0.000 claims description 4
- GOQBRHRXWRUDDK-UHFFFAOYSA-N 3,3-dimethyl-2-(3-morpholin-4-ylphenyl)-2,4-dihydro-1H-quinoline-6-carboxamide Chemical compound CC1(C)CC2=CC(C(N)=O)=CC=C2NC1C(C=1)=CC=CC=1N1CCOCC1 GOQBRHRXWRUDDK-UHFFFAOYSA-N 0.000 claims description 4
- JZXAENXIMDWBJA-UHFFFAOYSA-N 3,3-dimethyl-2-(4-morpholin-4-ylphenyl)-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=C1)=CC=C1N1CCOCC1 JZXAENXIMDWBJA-UHFFFAOYSA-N 0.000 claims description 4
- HJOFOAAWRZYEHO-UHFFFAOYSA-N 3,3-dimethyl-2-[3-(2-oxo-3-phenylimidazolidin-1-yl)phenyl]-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=1)=CC=CC=1N(C1=O)CCN1C1=CC=CC=C1 HJOFOAAWRZYEHO-UHFFFAOYSA-N 0.000 claims description 4
- QHVZCXOESBEJHT-UHFFFAOYSA-N 3,3-dimethyl-2-[3-(phenylcarbamoyl)phenyl]-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=1)=CC=CC=1C(=O)NC1=CC=CC=C1 QHVZCXOESBEJHT-UHFFFAOYSA-N 0.000 claims description 4
- DIWZCLUWUZQSMO-UHFFFAOYSA-N 6-fluoro-3,3-dimethyl-n-methylsulfonyl-2-(3-morpholin-4-ylphenyl)-2,4-dihydro-1h-quinoline-5-carboxamide Chemical compound CC1(C)CC(C(=C(F)C=C2)C(=O)NS(C)(=O)=O)=C2NC1C(C=1)=CC=CC=1N1CCOCC1 DIWZCLUWUZQSMO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 claims description 4
- ZUWYFMRCISCHLZ-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-3,3-dimethyl-2,4-dihydro-1H-quinoline-6-carboxamide Chemical compound CC1(C)CC2=CC(C(N)=O)=CC=C2NC1C1=CC(F)=CC(F)=C1 ZUWYFMRCISCHLZ-UHFFFAOYSA-N 0.000 claims description 3
- GOVXIXQFCLMLMI-UHFFFAOYSA-N 2-(3-chloro-5-morpholin-4-ylphenyl)-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=1)=CC(Cl)=CC=1N1CCOCC1 GOVXIXQFCLMLMI-UHFFFAOYSA-N 0.000 claims description 3
- MCLHCCWGHVPKTG-UHFFFAOYSA-N 2-(3-fluoro-5-pyrrolidin-1-ylphenyl)-3,3-dimethyl-2,4-dihydro-1H-quinoline-6-carboxamide Chemical compound CC1(C)CC2=CC(C(N)=O)=CC=C2NC1C(C=1)=CC(F)=CC=1N1CCCC1 MCLHCCWGHVPKTG-UHFFFAOYSA-N 0.000 claims description 3
- NUMNHHQYZUZPEW-UHFFFAOYSA-N 2-(5-fluoro-2-methylphenyl)-3,3-dimethyl-2,4-dihydro-1H-quinoline-6-carboxamide Chemical compound CC1=CC=C(F)C=C1C1C(C)(C)CC2=CC(C(N)=O)=CC=C2N1 NUMNHHQYZUZPEW-UHFFFAOYSA-N 0.000 claims description 3
- DZCBADGHCFBNLS-UHFFFAOYSA-N 2-[2-(methanesulfonamido)phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C1=CC=CC=C1NS(C)(=O)=O DZCBADGHCFBNLS-UHFFFAOYSA-N 0.000 claims description 3
- KNBUYTVVTLUTQK-UHFFFAOYSA-N 2-[3-(1-amino-2-methylpropan-2-yl)oxyphenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound NCC(C)(C)OC1=CC=CC(C2C(CC3=CC(=CC=C3N2)C(O)=O)(C)C)=C1 KNBUYTVVTLUTQK-UHFFFAOYSA-N 0.000 claims description 3
- QNMAWYINEBKKFS-UHFFFAOYSA-N 2-[3-(2-carboxypropan-2-ylamino)phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound OC(=O)C(C)(C)NC1=CC=CC(C2C(CC3=CC(=CC=C3N2)C(O)=O)(C)C)=C1 QNMAWYINEBKKFS-UHFFFAOYSA-N 0.000 claims description 3
- SLJXZYLUHXCSNJ-UHFFFAOYSA-N 2-[3-(6-chloro-3,3-dimethyl-2,4-dihydro-1h-quinolin-2-yl)anilino]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC1=CC=CC(C2C(CC3=CC(Cl)=CC=C3N2)(C)C)=C1 SLJXZYLUHXCSNJ-UHFFFAOYSA-N 0.000 claims description 3
- BWYJXUGSHBJVKZ-UHFFFAOYSA-N 2-[3-(6-cyano-3,3-dimethyl-2,4-dihydro-1h-quinolin-2-yl)anilino]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC1=CC=CC(C2C(CC3=CC(=CC=C3N2)C#N)(C)C)=C1 BWYJXUGSHBJVKZ-UHFFFAOYSA-N 0.000 claims description 3
- NRKFDNMTMIAPON-UHFFFAOYSA-N 2-[3-(benzenesulfonylcarbamoyl)phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=1)=CC=CC=1C(=O)NS(=O)(=O)C1=CC=CC=C1 NRKFDNMTMIAPON-UHFFFAOYSA-N 0.000 claims description 3
- PDVSJUFDJJDASX-UHFFFAOYSA-N 2-[3-(benzylcarbamoylamino)phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical group CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=1)=CC=CC=1NC(=O)NCC1=CC=CC=C1 PDVSJUFDJJDASX-UHFFFAOYSA-N 0.000 claims description 3
- JKRAMJLOPFIBFW-UHFFFAOYSA-N 2-[3-[(3-fluorobenzoyl)amino]phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(F)=C1 JKRAMJLOPFIBFW-UHFFFAOYSA-N 0.000 claims description 3
- FTHGXSPGKJLTPH-UHFFFAOYSA-N 2-[3-[(4-fluorobenzoyl)amino]phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=1)=CC=CC=1NC(=O)C1=CC=C(F)C=C1 FTHGXSPGKJLTPH-UHFFFAOYSA-N 0.000 claims description 3
- BYHIWSCAKDGULH-UHFFFAOYSA-N 2-[3-[carbamoyl(methyl)amino]phenyl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound NC(=O)N(C)C1=CC=CC(C2C(CC3=CC(=CC=C3N2)C(O)=O)(C)C)=C1 BYHIWSCAKDGULH-UHFFFAOYSA-N 0.000 claims description 3
- MNLBRYXXTISZLX-UHFFFAOYSA-N 2-[5-(4-tert-butylphenyl)pyridin-3-yl]-3,3-dimethyl-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CN=CC(C2C(CC3=CC(=CC=C3N2)C(O)=O)(C)C)=C1 MNLBRYXXTISZLX-UHFFFAOYSA-N 0.000 claims description 3
- PSPDTOJCNIBEFO-UHFFFAOYSA-N 3,3-dimethyl-2-[3-(2-oxoimidazolidin-1-yl)phenyl]-2,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound CC1(C)CC2=CC(C(O)=O)=CC=C2NC1C(C=1)=CC=CC=1N1CCNC1=O PSPDTOJCNIBEFO-UHFFFAOYSA-N 0.000 claims description 3
- DQMDAOAYWYKFDM-UHFFFAOYSA-N 3,3-dimethyl-n-methylsulfonyl-2-(3-morpholin-4-ylphenyl)-2,4-dihydro-1h-quinoline-6-carboxamide Chemical compound CC1(C)CC2=CC(C(=O)NS(C)(=O)=O)=CC=C2NC1C(C=1)=CC=CC=1N1CCOCC1 DQMDAOAYWYKFDM-UHFFFAOYSA-N 0.000 claims description 3
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- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- PVURAUIMVICLOH-UHFFFAOYSA-M zinc;cyclohexane;bromide Chemical compound Br[Zn+].C1CC[CH-]CC1 PVURAUIMVICLOH-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010071760 | 2010-04-14 | ||
| PCT/EP2011/055473 WO2011128251A1 (fr) | 2010-04-14 | 2011-04-08 | Nouveaux dérivés de 3,3-diméthyltétrahydroquinoléine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2012011780A true MX2012011780A (es) | 2012-11-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2012011780A MX2012011780A (es) | 2010-04-14 | 2011-04-08 | Nuevos derivados de 3,3-dimetil tetrahidroquinolina. |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8344137B2 (fr) |
| EP (1) | EP2558449B1 (fr) |
| JP (1) | JP2013523850A (fr) |
| KR (1) | KR101726469B1 (fr) |
| AR (1) | AR081072A1 (fr) |
| BR (1) | BR112012026338A2 (fr) |
| CA (1) | CA2795387C (fr) |
| ES (1) | ES2454866T3 (fr) |
| MX (1) | MX2012011780A (fr) |
| RU (1) | RU2603276C2 (fr) |
| TW (1) | TW201139379A (fr) |
| WO (1) | WO2011128251A1 (fr) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8592594B2 (en) * | 2010-07-02 | 2013-11-26 | Hoffmann-La Roche Inc. | Tetrahydro-quinoline derivatives |
| US8546427B2 (en) | 2010-10-20 | 2013-10-01 | Hoffmann-La Roche Inc. | Tetrahydroquinoline derivatives |
| US8809369B2 (en) * | 2011-01-26 | 2014-08-19 | Hoffmann-La Roche Inc. | Tetrahydroquinoline derivatives |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| US20150027041A1 (en) * | 2013-03-07 | 2015-01-29 | Blue River Technology, Inc. | System and method for plant cauterization |
| CA2905242C (fr) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Composes indoliques activant l'ampk |
| CN103539381B (zh) * | 2013-09-29 | 2015-04-08 | 北方工业大学 | 一种豆石混凝土用外加剂 |
| US10143703B2 (en) | 2014-01-02 | 2018-12-04 | Massachusetts Eye And Ear Infirmary | Treating ocular neovascularization |
| IL313498A (en) | 2014-10-06 | 2024-08-01 | Vertex Pharma | Modulators of the cystic fibrosis transmembrane conductance regulator |
| ITUB20151256A1 (it) | 2015-05-28 | 2016-11-28 | Olon Spa | Processo industriale per la preparazione di enzalutamide |
| EP3436446B1 (fr) | 2016-03-31 | 2023-06-07 | Vertex Pharmaceuticals Incorporated | Modulateurs du régulateur de la conductance transmembranaire de la fibrose kystique |
| HRP20211683T1 (hr) | 2016-09-30 | 2022-03-04 | Vertex Pharmaceuticals Incorporated | Modulator transmembranskog regulatora provodljivosti cistične fibroze, farmaceutski pripravci, postupci liječenja, i postupak za pripravu modulatora |
| MX2021013639A (es) | 2016-12-09 | 2022-09-30 | Vertex Pharma | Forma cristalina del compuesto 1, un modulador del regulador de conductancia transmembrana de fibrosis quística, procesos para su preparación, composiciones farmacéuticas del compuesto 1, y su uso en el tratamiento de fibrosis quística. |
| GB201622345D0 (en) * | 2016-12-29 | 2017-02-15 | Redag Crop Prot Ltd | Agricultural chemicals |
| AU2018279646B2 (en) | 2017-06-08 | 2023-04-06 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| AU2018304168B2 (en) | 2017-07-17 | 2023-05-04 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| TWI799435B (zh) | 2017-08-02 | 2023-04-21 | 美商維泰克斯製藥公司 | 製備化合物之製程 |
| WO2019079760A1 (fr) | 2017-10-19 | 2019-04-25 | Vertex Pharmaceuticals Incorporated | Formes cristallines et compositions de modulateurs de cftr |
| US11465985B2 (en) | 2017-12-08 | 2022-10-11 | Vertex Pharmaceuticals Incorporated | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
| WO2019200246A1 (fr) | 2018-04-13 | 2019-10-17 | Alexander Russell Abela | Modulateurs du régulateur de la conductance transmembranaire de la fibrose kystique, compositions pharmaceutiques, procédés de traitement et procédé de fabrication du modulateur |
| JP2023526625A (ja) | 2020-05-19 | 2023-06-22 | キャリーオペ,インク. | Ampkアクチベーター |
| CN116390925A (zh) | 2020-06-26 | 2023-07-04 | 卡尔优普公司 | Ampk活化剂 |
| US12404348B2 (en) | 2021-11-19 | 2025-09-02 | The Brigham And Women's Hospital, Inc. | Bifunctional chimeric molecules for labeling of kinases with target binding moieties and methods of use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7138412B2 (en) * | 2003-03-11 | 2006-11-21 | Bristol-Myers Squibb Company | Tetrahydroquinoline derivatives useful as serine protease inhibitors |
| RU2375354C2 (ru) * | 2003-12-20 | 2009-12-10 | Мерк Патент Гмбх | Производные 2-(гетеро)арил-замещенных тетрагидрохинолинов |
| AU2009296820B2 (en) * | 2008-09-26 | 2014-03-20 | Merck Sharp & Dohme Llc | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2011009523A1 (fr) * | 2009-07-24 | 2011-01-27 | Merck Patent Gmbh | Utilisation de leg5 comme biomarqueur dans les tumeurs thoraciques rares |
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2011
- 2011-04-07 US US13/081,527 patent/US8344137B2/en not_active Expired - Fee Related
- 2011-04-08 EP EP11715896.4A patent/EP2558449B1/fr not_active Not-in-force
- 2011-04-08 JP JP2013504203A patent/JP2013523850A/ja active Pending
- 2011-04-08 WO PCT/EP2011/055473 patent/WO2011128251A1/fr not_active Ceased
- 2011-04-08 RU RU2012146444/04A patent/RU2603276C2/ru not_active IP Right Cessation
- 2011-04-08 MX MX2012011780A patent/MX2012011780A/es active IP Right Grant
- 2011-04-08 KR KR1020127029575A patent/KR101726469B1/ko not_active Expired - Fee Related
- 2011-04-08 BR BR112012026338A patent/BR112012026338A2/pt not_active Application Discontinuation
- 2011-04-08 CA CA2795387A patent/CA2795387C/fr not_active Expired - Fee Related
- 2011-04-08 ES ES11715896.4T patent/ES2454866T3/es active Active
- 2011-04-11 TW TW100112503A patent/TW201139379A/zh unknown
- 2011-04-12 AR ARP110101228A patent/AR081072A1/es unknown
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2012
- 2012-09-28 US US13/630,057 patent/US8586747B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR101726469B1 (ko) | 2017-04-12 |
| HK1176608A1 (en) | 2013-08-02 |
| TW201139379A (en) | 2011-11-16 |
| AR081072A1 (es) | 2012-06-06 |
| EP2558449A1 (fr) | 2013-02-20 |
| US20110257151A1 (en) | 2011-10-20 |
| RU2012146444A (ru) | 2014-05-20 |
| US8586747B2 (en) | 2013-11-19 |
| KR20130066607A (ko) | 2013-06-20 |
| EP2558449B1 (fr) | 2014-03-05 |
| BR112012026338A2 (pt) | 2016-07-19 |
| WO2011128251A1 (fr) | 2011-10-20 |
| US8344137B2 (en) | 2013-01-01 |
| RU2603276C2 (ru) | 2016-11-27 |
| ES2454866T3 (es) | 2014-04-11 |
| JP2013523850A (ja) | 2013-06-17 |
| CA2795387C (fr) | 2018-01-02 |
| US20130023518A1 (en) | 2013-01-24 |
| CA2795387A1 (fr) | 2011-10-20 |
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